The United States Postal Service (USPS) provides an effective way ship items between a source and a destination. The USPS classifies all types of mail and charges various postage rates accordingly. The classifications range from automated flat to priority mail and express post, with many classes in-between. Even within automated flat, many subclasses such as first class or standard mail exist. However, in contrast to other classes of mail, automated flat mail is handled by a machine at the mail distribution center. Accordingly, all shipping items destined for automated flat processing must meet certain requirements addressing size, weight, and/or flexibility. Further, items that are not flexible may need to be secured for shipping. These challenges make it difficult to ship items having even minimal thickness using automated flat mail.